Electron transfer initiated heterogenerative cascade cyclizations: Polyether synthesis under nonacidic conditions

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2489-2492

  Kumar, V Satish ^a   Aubele, Danielle L ^a   Floreancig, Paul E ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; ETHER DERIVATIVE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; TETRAHYDROFURAN;

ARTICLE; CHEMISTRY; CYCLIZATION; ELECTRON; OXIDATION REDUCTION REACTION; SYNTHESIS;

CYCLIZATION; ELECTRONS; EPOXY COMPOUNDS; ETHERS; FURANS; HETEROCYCLIC COMPOUNDS; OXIDATION-REDUCTION;

EID: 0001378378     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0261074     Document Type: Article

References (38)

1. Tietze, L. F. Chem. Rev. 1996, 96, 115.
2. (a) Johnson, W. S. Tetrahedron 1991, 47, R11.
3. (b) Ishihara, K.; Ishibashi, H.; Yamamoto, H. J. Am. Chem. Soc. 2002, 124, 3647.
4. (c) Huang, A. X.; Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 9999 and references therein.
5. (a) Koert, U. Synthesis 1995, 115.
6. (b) McDonald, F. E.; Bravo, F.; Wang, X.; Wei, X.; Toganoh, M.; Rodríguez, R.; Do, B.; Neiwart, W. A.; Hardcastle, K. I. J. Org. Chem. 2002, 67, 2515.
7. (c) McDonald, F. E.; Wang, X.; Do, B.; Hardcastle, K. I. Org. Lett. 2000, 2, 2917.
8. (d) Xiong, Z.; Corey, E. J. J. Am. Chem. Soc. 2000, 122, 4831.
9. (e) Still, W. C.; Romero, A. G. J. Am. Chem. Soc. 1986, 108, 2105.
10. (f) Schreiber, S. L.; Sammakia, T.; Hulin, B.; Schulte, G. J. Am. Chem. Soc. 1986, 108, 2106.
11. Wender, P. A.; Miller, B. L. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 27-66.
12. For an excellent illustration of this strategy, see: Khan, N.; Xiao, H.; Zhang, B.; Cheng, X.; Mootoo, D. R. Tetrahedron 1999, 55, 8303.
13. Kumar, V. S.; Floreancig, P. E. J. Am. Chem. Soc. 2001, 123, 3842.
14. For discussions of the reactivity patterns of radical cations, see: (a) Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2551.
15. (b) Baciocchi, E.; Bietti, M.; Lanzalunga, O. Acc. Chem. Res. 2000, 33, 243.
16. (c) Schmittel, M.; Ghorai, M. K. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2, Organic Molecules, pp 5-54.
17. (d) Mella, M.; Fagnoni, M.; Freccero, M.; Fasani, E.; Albini, A. Chem. Soc. Rev. 1998, 27, 81.
18. (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504.
19. (b) Hoppe, R.; Scharf, H.-D. Synthesis 1995, 1447.
20. Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
21. Kumar, V. S.; Aubele, D. L.; Floreancig, P. E. Org. Lett. 2001, 3, 4123.
22. (a) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
23. (b) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806.
24. For a related approach to the enantioselective synthesis of bisepoxides, see ref 3b.
25. Barresi, F.; Hindsgaul, O. J. Am. Chem. Soc. 1991, 113, 9376.
26. (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5675.
27. (b) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
28. (a) Na, J.; Houk, K. N.; Shevlin, C. G.; Janda, K. D.; Lerner, R. A. J. Am. Chem. Soc. 1993, 115, 8453.
29. (b) Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
30. Koide, K.; Finkelstein, J. M.; Ball, Z.; Verdine, G. L. J. Am. Chem. Soc. 2001, 123, 398.
31. (a) Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
32. (b) Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
33. Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
34. The chloro-ether was prepared by bubbling anhydrous HCl gas through a solution of acetaldehyde and p-trifluoromethylbenzyl alcohol in benzene at 0 °C for 6 h.
35. Liotta, L. J.; Dombi, K. L.; Kelley, S. A.; Targontsidis, S.; Morin, A. M. Tetrahedron Lett. 1997, 38, 7833.
36. (a) Stanek, J.; Marek, M.; Jary, J. Carbohydr. Res. 1978, 64, 315.
37. (b) Grethe, G.; Mitt, T.; Williams, T. H.; Uskokovic, M. J. Org. Chem. 1983, 48, 5309.
38. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 738.